54-year-old lost friends, was sued by family after first startup went bankrupt—she sold her second company for $745 million

It’s one thing for your company to go bankrupt. But Kass and Mike Lazerow say they lost friends because of it too.

In August 2000, just two months after the now defunct e-commerce retailer Chipshot completed its acquisition of the Lazerows’ golf score tracker, Golf.com, for a reported $250,000 in cash and 3 million shares of Chipshot stock, Mike says he got a call from the Chipshot CEO.

Chipshot was headed toward bankruptcy, Mike, now 51, says. All the stock Mike, Kass and their investors had received in the deal was worthless.

“It sucked,” Kass, 54, tells CNBC Make It. “We had to look [our investors] in the eye and say, ‘we basically failed.’”

Not only did Mike and Kass have $25,000 of their own savings invested in the company, but the first $1 million they raised came from family members and friends, Kass says. They had to tell “pseudo uncles and aunts,” parents and siblings that their money was gone.